US4224239A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for preparing optically active amino acid or mandelic acid
Assignee: Nippon Kayaku Co Ltd
•
Filing: 1979-04-24
•
Granted: 1980-09-23
•
Expires: 1999-04-24
Abstract
Abstract Two optically active amino acid-mandelic acid complexes are obtained by interacting in a solvent under pH conditions of 1.0-4.0 an amino acid expressed by a general formula ##STR1## (in which R represents a methyl group, an ethyl group or a methylthioethyl group) and mandelic acid, one of the acids being an optically active substance and the other being a racemic modification, and optically resolving the resulting complexes into two diastereoisomers by using solubility difference therebetween. The optically active complexes are each decomposed by means of an acid, a strongly acidic ion-exchange resin, or a weakly basis ion-exchange resin to obtain optically active amino acids or optically active mandelic acid.
Inventors
- 👤 Yasuhisa Tashiro
- 👤 Takashi Nagashima
- 👤 Shigeru Aoki
- 👤 Rinzo Nishizawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 16:41
CPC Classifications
C; C07; C07C; C07C59/00; C07C59/40; C07C59/42; C07C59/48; C07C59/50
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
135 words
A process for preparing an optically active amino acid-mandelic acid complex characterized by reacting in a solvent, at a pH of 1.0 to 4.0 and at a temperature of room 50° C. to the boiling point of the solvent, an optically active isomer of an amino acid of the formula: ##STR4## wherein R is a methyl, ethyl or methylthioethyl group, with racemic mandelic acid in an amount of 0.3 to 6.0 equivalents per unit equivalent to said amino acid, or a raceme of said amino acid with an optically active isomer of mandelic acid in an amount of 0.3 to 6.0 equivalents per unit equivalent to said amino acid, and crystallizing and separating the thus resulting complexes by selective crystallization of the less soluble isomer complex at a temperature of from 0° to 50° C.
Claim 2
Dependent Claim
135 words
A process for preparing an optically active amino acid-mandelic acid complex characterized by reacting in a solvent, at a pH of 1.0 to 4.0 and at a temperature of room 50° C. to the boiling point of the solvent, an optically active isomer of an amino acid of the formula: ##STR4## wherein R is a methyl, ethyl or methylthioethyl group, with racemic mandelic acid in an amount of 0.3 to 6.0 equivalents per unit equivalent to said amino acid, or a raceme of said amino acid with an optically active isomer of mandelic acid in an amount of 0.3 to 6.0 equivalents per unit equivalent to said amino acid, and crystallizing and separating the thus resulting complexes by selective crystallization of the less soluble isomer complex at a temperature of from 0° to 50° C.
Claim 3
Dependent Claim
26 words
A process according to claim 1, wherein said solvent is a member selected from the group consisting of water, water-containing methanol, water-containing ethanol and water-containing acetone.
Claim 4
Dependent Claim
20 words
A process according to claim 1, wherein the concentration of said amino acid is 10-70% by weight of said solvent.
Claim 5
Dependent Claim
182 words
A process for preparing an optically active substance of the formula: ##STR5## wherein X is an amino group and R is a methyl, ethyl or methylthioethyl group, or X is hydroxy group and R is phenyl group; which process comprises reacting in a solvent, at a pH of 1.0 to 4.0 and at a temperature of from 50° C. to the boiling point of the solvent, an optically active isomer of an amino acid of the formula: ##STR6## wherein R is a methyl, ethyl or methylthioethyl group, with racemic mandelic acid in an amount of 0.3 to 6.0 equivalents per unit equivalent to said amino acid, or a raceme of said amino acid with an optically active isomer of mandelic acid in an amount of 0.3 to 6.0 equivalents per unit equivalent to said amino acid, crystallizing and separating the thus resulting complexes by selective crystallization, at a temperature of from 0° to 50° C., and decomposing each of the two crystallized optically active complexes thus resolved by adding an acid, a strongly acidic ion-exchange resin or a weak basic ion-exchange resin.
Claim 6
Dependent Claim
182 words
A process for preparing an optically active substance of the formula: ##STR5## wherein X is an amino group and R is a methyl, ethyl or methylthioethyl group, or X is hydroxy group and R is phenyl group; which process comprises reacting in a solvent, at a pH of 1.0 to 4.0 and at a temperature of from 50° C. to the boiling point of the solvent, an optically active isomer of an amino acid of the formula: ##STR6## wherein R is a methyl, ethyl or methylthioethyl group, with racemic mandelic acid in an amount of 0.3 to 6.0 equivalents per unit equivalent to said amino acid, or a raceme of said amino acid with an optically active isomer of mandelic acid in an amount of 0.3 to 6.0 equivalents per unit equivalent to said amino acid, crystallizing and separating the thus resulting complexes by selective crystallization, at a temperature of from 0° to 50° C., and decomposing each of the two crystallized optically active complexes thus resolved by adding an acid, a strongly acidic ion-exchange resin or a weak basic ion-exchange resin.
Claim 7
Dependent Claim
26 words
A process according to claim 4, wherein said solvent is a member selected from the group consisting of water, water-containing methanol, water-containing ethanol and water-containing acetone.
Claim 8
Dependent Claim
24 words
A process according to claim 4, wherein the concentration of said amino acid is in the range of 10-70% by weight of said solvent.
Claim 9
Dependent Claim
15 words
A process according to claim 4, wherein said acid is hydrochloric acid or sulfuric acid.
Claim 10
Dependent Claim
21 words
A process according to claim 4, wherein said strongly acidic ion-exchange resin is a styrene.divinylbenzene copolymer introduced with sulfonic acid groups.
Claim 11
Dependent Claim
26 words
A process according to claim 4, wherein said weakly basic ion-exchange resin is a styrene.divinylbenzene copolymer introduced with amine, acrylic resin, phenolic resin or epoxy resin.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-09-23 | 1984-03-24 | 1984-09-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-23 | 1988-03-24 | 1988-09-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-23 | 1992-03-24 | 1992-09-23 | $7700.00 | Window Closed / Lapsed |